2-Methoxyethylamine → HCID 68157994, compound

HRID 243171Notes

Reaction equation

HRID 243171 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([F:11])[C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.[CH3:18][O:19][CH2:20][CH2:21][NH2:22].CCN(C(C)C)C(C)C>CC#N>[F:11][C:4]1[C:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[C:2]([NH:22][CH2:21][CH2:20][O:19][CH3:18])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 81531DiisopropylethylamineHCID 68157421HCID 68157421, compound

Product 1

HCID 68157994HCID 68157994, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2-(2-chloro-6-fluoro-3-nitrophenyl)pyridine* (618 mg, 2.6 mmol), 2-methoxyethylamine (0.23 mL, 2.6 mmol) and DIPEA (0.48 mL, 2.7 mmol) in MeCN (5 mL) was stirred for 1.5 h at 0° C. After warming to RT, the volatiles were removed in vacuo. The resulting residue was purified by column chromatography (Si—PPC, gradient 0-70% EtOAc/cyclohexane) to afford the title compound as a yellow oil (414 mg, 54%). LCMS (Method C): RT 2.95 min [M+H]+ 292. 1H NMR (CDCl3, 400 MHz): δ 8.73 (1H, ddd, J=5.0, 2.0, 1.0 Hz), 8.47 (1H, bs), 8.26 (1H, dd, J=9.5, 6.0 Hz), 7.79 (1H, ddd, 8.0, 8.0, 2.0 Hz), 7.45-7.43 (1H, m), 7.32 (1H, ddd, J=7.5, 5.0, 1.0 Hz), 6.52 (1H, dd, 9.5, 8.0 Hz), 3.29-3.26 (2H, m), 3.28 (3H, s), 2.63-2.60 (2H, m)

Workup

  1. temperatureAfter warming to RT
  2. customthe volatiles were removed in vacuo
  3. customThe resulting residue was purified by column chromatography (Si—PPC, gradient 0-70% EtOAc/cyclohexane)

Sources & evidence

ORD record
ord-76b03ea8c86445a084017d3acbf3e53b
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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